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Cytotoxic Analogs of Pyridine Nucleotide Coenzymes

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Antineoplastic and Immunosuppressive Agents

Abstract

NAD+ and NADP+ are among the most important coenzymes in biological systems. Aberrations in the regulation of their synthesis and metabolism could have profound effects on living systems because of the central role played by these coenzymes in intermediary metabolism.

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References

  • Baccino, F. M.: Heart and liver cloudy swelling by 6-aminonicotinamide (6-AN) in rats. Sperimentale 112, 61–73 (1962).

    PubMed  CAS  Google Scholar 

  • Branster, M. V., Morton, R. K.: Comparative rates of synthesis of diphosphopyridine nucleotide by normal and tumor tissue from mouse mammary gland: Studies with isolated nuclei. Biochem. J. 63, 640–646 (1956).

    PubMed  CAS  Google Scholar 

  • Brunnemann, A., Coper, H., Neubert, D.: Biosynthese und Wirkung des 6-Aminonicotin- amid-adenindinucleotids (6-ANAD). Naunyn-Schmiedeberg’s Arch. exp. Path. Pharmak. 246, 437–451 (1964).

    CAS  Google Scholar 

  • Chamberlain, J. G.: Effects of acute vitamin replacement therapy on 6-aminonicotinamide induced cleft palate late in rat pregnancy. Proc. Soc. exp. Biol. (N. Y.) 124, 888–890 (1966).

    Google Scholar 

  • Coper, H., Netjbert, D.: Effect of 6-amino NAD and other NAD analogues on the formation of NADH ~ P and its transphosphorylation to ATP. Biochim. biophys. Acta (Amst.) 82, 167–170 (1964).

    CAS  Google Scholar 

  • Dietrich, L. S.: Augmentation of 6-aminonicotinamide antagonism of tumor growth by compounds with estrogenic activity. Cancer Res. 24, 61–63 (1964).

    PubMed  CAS  Google Scholar 

  • Dietrich, L. S., Friedland, I. M.: 6-Aminonicotinamide and 6-aminonicotinic acid metabolism in nucleated and non-nucleated erythrocytes. Arch. Biochem. Biophys. 88, 313–317 (1960).

    Article  PubMed  CAS  Google Scholar 

  • Dietrich, L. S., Friedland, I. M., Kaplan, L. A.: Pyridine nucleotide metabolism: Mechanism of action of the niacin antagonist 6-aminonicotinamide. J. biol. Chem. 233, 964–968 (1958a).

    PubMed  CAS  Google Scholar 

  • Dietrich, L. S., Kaplan, L. A., Friedland, I. M., Martin, D. S.: Quantitative biochemical differences between tumor and host tissue. VI. 6-Aminonicotinamide antagonism of DPN- dependent enzymatic systems. Cancer Res. 18, 1272–1280 (1958b).

    PubMed  CAS  Google Scholar 

  • Dietrich, L. S., Martin, D. S.: Augmentation of 6-aminonicotinamide antagonism of DPN- dependent enzymatic systems by diethylstilbesterol. Cancer Res. 21, 361–364 (1961).

    PubMed  CAS  Google Scholar 

  • Dietrich, L. S., Mtjniz, O., Farinas, B., Franklin, L.: 6-Aminonicotinamide-14C utilization by the 755 tumor and host liver tissue. Cancer Res. 28, 1652–1654 (1968).

    PubMed  CAS  Google Scholar 

  • Glock, G. E., Mclean, P.: Levels of oxidized and reduced diphosphopyridine nucleotide and triphosphopyridine nucleotide in tumours. Biochem. J. 65, 413–416 (1957).

    PubMed  CAS  Google Scholar 

  • Greengard, P., Sigg, E. B., Fratta, I., Zak, S. B.: Prevention and remission by adrenocortical steroids of nicotinamide deficiency disorders and of 6-aminonicotinamide toxicity in rats and dogs. J. Pharmacol, exp. Ther. 154, 624–631 (1966).

    CAS  Google Scholar 

  • Herken, H., Senft, G., Zemisch, B.: Die Einschränkung des tubulären Natrium- und Kaliumtransportes durch Biosynthese 6-Aminonicotinsäureamid enthaltender Nucleotide. Naunyn- Schmiedeberg’s Arch. exp. Path. Pharmak. 249, 54–70 (1964).

    CAS  Google Scholar 

  • Herken, H., Senft, G., Zemisch, B.: Der Einfluß von 6-Aminonicotinsäureamid auf die Verteilung der Natrium- und Kaliumionen zwischen dem extra- und intracellulären Raum in der Leber und der Skelettmuskulatur. Naunyn-Schmiedeberg’s Arch. exp. Path. Pharmak. 253, 364–371 (1966).

    Article  CAS  Google Scholar 

  • Herter, F. P., Weissman, S. G., Thompson, H. G., Jr., Hyman, G., Martin, D. S.: Clinical experience with 6-aminonicotinamide. Cancer Res. 21, 31–37 (1961).

    PubMed  CAS  Google Scholar 

  • Hogeboom, G. H., Schneider, W. C.: Cytochemical studies. VI. The synthesis of diphosphopyridine nucleotide by liver cell nuclei. J. biol. Chem. 197, 611–620 (1952).

    PubMed  CAS  Google Scholar 

  • Jedeikin, L. A., Weinhotjse, S.: Metabolism of neoplastic tissue. VI. Assay of oxidized and reduced diphosphopyridine nucleotide in normal and neoplastic tissues. J. biol. Chem. 213, 271–280 (1955).

    PubMed  CAS  Google Scholar 

  • Johnson, W. J., Mccoll, J. D.: 6-Aminonicotinamide — A potent nicotinamide antagonist. Science 122, 834 (1955).

    Article  PubMed  CAS  Google Scholar 

  • Johnson, W. J., Mccoll, J. D.: Antimetabolite activity of 6-aminonicotinamide. Fed. Proc. 15, 284 (1956).

    Google Scholar 

  • Kaplan, N. O., Goldin, A., Humphreys, S. R., Ciotti, M. R., Venditti, J. M.: Significance of enzymatically catalyzed exchange reactions in chemotherapy. Science 120, 437–440 (1954).

    Article  PubMed  CAS  Google Scholar 

  • Martin, D. S., Dietrich, L. S., Ftjgmann, R. A.: Hormonal augmentation of antimetabolite chemotherapy. Proc. Soc. exp. Biol. (N.Y.) 103, 58–60 (1960).

    CAS  Google Scholar 

  • Morton, R. K.: Enzymic synthesis of coenzyme I in relation to chemical control of cell growth. Nature (Lond.) 181, 540–542 (1958).

    Article  CAS  Google Scholar 

  • Pullman, B., Pullman, A.: Comment on the 6-aminonicotinamide antagonism of DPN- dependent enzymatic systems. Cancer Res. 19, 337–338 (1959).

    PubMed  CAS  Google Scholar 

  • Redetzki, H. M., Alvarez- O’bourke, F.: 6-Aminonicotinamide, a central nervous system depressant. J. Pharmacol, exp. Ther. 187, 173–178 (1962).

    Google Scholar 

  • Shapiro, D. M., Dietrich, L. S., Shils, M. E.: Quantitative biochemical differences between tumor and host as a basis for cancer chemotherapy. V. Niacin and 6-aminonicotinamide. Cancer Res. 17, 600–604 (1957).

    PubMed  CAS  Google Scholar 

  • Sund, H.: The pyridine nucleotide coenzymes. In: Singer, T. P. (Ed.): Biological oxidations, pp. 603–639. New York: Interscience 1968.

    Google Scholar 

  • Woods, M., Burk, D.: Formation of glycolytic inhibitor from 6-aminonicotinamide by ascites tumor cells in vivo and in vitro, and metabolic requirements for formation of this inhibitor. Biochem. Z. 888, 381–392 (1963).

    Google Scholar 

  • Zatman, L. J., Kaplan, N. O., Colowick, S. P.: Inhibition of spleen diphosphopyridine nucleotidase by nicotinamide, an exchange reaction. J. biol. Chem. 200, 197–212 (1953).

    PubMed  CAS  Google Scholar 

  • Zatman, L. J., Kaplan, N. O., Colowick, S. P., Ciotti, M. M.: The isolation and properties of the isonicotinic acid hydrazide analogue of diphosphopyridine nucleotide. J. biol. Chem. 209, 467–484 (1954).

    PubMed  CAS  Google Scholar 

Further References

  • Harris, T., Netjhoff, V.: Biosynthese, Verteilung und Ausscheidung von 3-Acetyl-6-pyridin, einem Metaboliten des 3-Acetylpyridins. Naunyn-Schmiedebergs Arch. exp. Path. Pharmak. 253, 221–234 (1966).

    CAS  Google Scholar 

  • Herken, H.: Drug-Induced Pathobiotic Effects. In: Proc. 3rd Intern. Pharmacol. Meeting, Vol. 4: Mechanism of Drug Toxicity, pp. 3–21. Oxford-New York: Pergamon Press 1968 a.

    Google Scholar 

  • Herken, H.: Functional Discorders of the Brain Induced by Synthesis of Nucleotides Containing 3-Acetylpyridine. Z. klin. Chem. klin. Biochem. 6, 357–367 (1968 b).

    Google Scholar 

  • Herken, H., Neuhoff, V.: Mikroanalytischer Nachweis von Acetylpyridin-adenin-dinucleotid und Acetylpyridin- adenindinucleotid- phosphat im Gehirn. Hoppe-Seylers Z. physiol. Chem. 331, 85–94 (1963).

    Article  CAS  Google Scholar 

  • Herken, H., Timmler, R.: Kinetik der Dihydrofolsäurereduktase aus Rattenleber und -gehirn mit 3-APADPH und H+ als Wasserstoffdonator. Naunyn-Schmiedebergs Arch. exp. Path. Pharmak. 250, 293–301 (1965).

    CAS  Google Scholar 

  • Neuhoff, V., Köhler, F.: Biochemische Analyse des Stoffwechsels von 3-Acetylpyridin. Naunyn-Schmiedebergs Arch. Pharmak. exp. Path. 254, 301–326 (1966).

    CAS  Google Scholar 

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Dietrich, L.S. (1975). Cytotoxic Analogs of Pyridine Nucleotide Coenzymes. In: Sartorelli, A.C., Johns, D.G. (eds) Antineoplastic and Immunosuppressive Agents. Handbuch der experimentellen Pharmakologie / Handbook of Experimental Pharmacology, vol 38 / 2. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-65806-8_26

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  • DOI: https://doi.org/10.1007/978-3-642-65806-8_26

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-65808-2

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